My first cave dives were with singles, since doubles weren't readily available, so doubles would be the first improvement. They were hard to dive, because our BCDs were on our chest, and you tended to roll if you weren't careful. The Back mounted BCD was a big improvement. I had actually switched to sidemount, before the backplate/wing came out.
Second was the made-for-cavediving-reel. We were using reels intended for other things, or made our own.
The advent of dry suits made a big difference. My first one was neoprene, because shell suits weren't out yet. When the shell suits came out, I switched to them.
Better lights were a big change. First it was the "super bright" Halogen lights. It was like someone had turned on the sun. However the bulb had to stay dry, so we used laboratory test tubes, which broke easily. We solved that by having custom, thick walled tubes made.
Then The HID came out and blew the Halogen away. The big problem with HID was the early ones were very fragile so the advent of LED lights solved that. The problem is they weren't as bright as HID lights.
Then came improvements in LED which made them as bright as HID.
The next big change was dive computers. The first ones actually were worse than dive tables, and got a lot of people bent. A nickname for the early ones was "Bend-O-Matic". I waited until they were actually safe before buying one. It was a 2 gas model, and at the time was great. That technology is still improving.
Then the scooter came along. The Faralon was the hot thing, but had motorcycle batteries, which tended to spill. That was solved by putting NiCad batteries in them, but they were expensive. I waited until the Tekna came out to get one. Then Gavin improved the Tekna, by making bigger battery tubes, still lead acid, but sealed to avoid spills. I got one of the first NiMh powered scooters, but the batteries didn't last long. Then I converted it to Lithium ion, and still use that, but some of the later generation ones are a lot better.
Actually I suspect the biggest "must have" piece of gear, was actually the cheapest. For a hint, look to the left of the text

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